A love affair in the extreme. A passionate and self-destructive story between two of the most extraordinary stars ever to pass through Hollywood. Frank Sinatra and Ava Gardner wrote one of the most compelling love stories of the 20th century, full of unbridled passion and explosive outbursts that stirred the mores of the time.

He was Ol’ Blue Eyes, velvet-voiced crooner and rumored confidant of the underworld. She was the sinful Ava, the most breathtaking woman to grace Hollywood’s golden age. Together, they created a tempestuous universe of champagne-soaked nights, volcanic passion, and heartbreak that glittered as brightly as it burned. What endured beyond the ruin was a singular, haunting love—and a car, now headed for auction, still carrying the scent of legend in its leather seats.

Frank Sinatra, then a married father of three, was captivated by Ava Gardner long before they met. She found him arrogant and far too slight for her taste in men. But fate had other ideas, as did the MGM backlots. Shared addictions to excess—booze, cigarettes, glamorous chaos—drew them together. On Valentine’s Day 1950, Sinatra confessed the affair to his wife, igniting a scandal that splashed across every paper in America. Their wedding in 1951 was modest, but their marriage was anything but. Fights were operatic, their passion radioactive. Friends recall flying ashtrays and couture flung from balconies. And yet, for all the spectacle, theirs was no mere dalliance—it was war and poetry combined.

Their story lives on in chrome and midnight paint: a 1957 Dual-Ghia Convertible, now up for auction. Midnight blue with cream-blue interiors and a canvas roof, it’s one of just 34 survivors out of 117 ever made. Sinatra gifted it to Gardner at the peak of their entanglement—a rolling testament to their love and volatility. Under the hood, a 361-cubic-inch D-500 V8 growls with promise. Within, power windows, electric brakes, and a Town & Country radio whisper of a time when luxury was not loud, but utterly assured.

Though they divorced in 1957, Sinatra never stopped loving her. He covered her hospital bills, managed her affairs, and never let the world forget who she had been to him. When she died in 1990, a letter from Frank lay open on her nightstand beside a fading photograph of the two. The house they once shared remained his until the end.

Today, that very car—restored to perfection and seen in films and concours d’elegance alike—is expected to fetch over half a million dollars. But no price can capture the myth it carries: the story of a love that seared, survived, and still glows beneath a waxed hood and polished fenders.

Because some affairs are more than romance. They are history on wheels.

The menu had everything: pathological jealousy, monumental fights, parallel affairs, endless late nights of drinking, jazz and abuse, and suicide attempts. And with all of it, moments of reconciliation and unbridled sex.